For over a decade, Jon Cryer captivated television audiences with his performance as Alan Harper in the CBS sitcom Two and a Half Men (2003–2015). His portrayal of the neurotic, financially struggling chiropractor earned him six Emmy nominations with two wins. Starring alongside Charlie Sheen and later Ashton Kutcher, Jon Cryer became a staple of primetime television, earning a reputation as one of the most dependable comedic actors of his generation.
Fast-forward a decade since the show ended, and many of today’s new television audiences are hardly familiar with the talented actor. However, while the end of Two and a Half Men marked a pivotal point in Jon Cryer’s career, it was far from his end. In the past decade, Cryer has remained busy, but not always in ways fans and audiences would have expected. Here’s a closer look at Jon Cryer’s life and career since his remarkable run on Two and a Half Men.
Jon Cryer’s Acting Career After Two and a Half Men
Having spent 12 seasons on the show, understandably, Jon Cryer took some well-deserved time off. Playing Alan Harper for over a decade had been both rewarding and exhausting. Towards the end of Two and a Half Men, Cryer reportedly earned $500,000 per episode, making him one of the highest-paid actors on television. With the series over, Cryer chose not to rush into another long-term sitcom commitment. Instead, Cryer took on more selective roles and made a surprising pivot into dramatic and genre-focused television.
Jon Cryer’s next major and iconic project came in 2019. Cryer was cast as Lex Luthor and first appeared as the supervillain in Supergirl (2019–2021). He reprised the role in several other The CW superhero TV series, including Batwoman (2019), The Flash (2019), Arrow (2020), and Legends of Tomorrow (2020). Although die-hard DC Comics fans were initially skeptical of Cryer’s casting, the actor’s chilling and complex performance ultimately won over critics and viewers. On the big screen, Cryer played a protective and morally grounded father in a dramatic role in Big Time Adolescence (2019). The film starred Pete Davidson, Griffin Gluck, and Sydney Sweeney.
Jon Cryer Has Been Working Behind the Camera
Jon Cryer made his directorial debut on Two and a Half Men in 2007 when he directed an episode of the show. Between that episode and the series finale, Cryer directed four additional episodes. Additionally, he directed the pilot episode of the CBS situational comedy-drama Mom and returned to direct another in 2016, following the end of Two and a Half Men. The following year, Cryer directed two episodes of the Netflix sitcom Disjointed.
Besides his directorial credits, Jon Cryer has raked in credits as a producer since the mid-1990s. However, he didn’t produce any project after 1998 until years after Two and a Half Men ended. In 2020, Cryer executive-produced the crime documentary The Forgotten West Memphis Three, which was based on the notorious West Memphis Three cases. In 2023, Jon Cryer launched the podcast series Lawyers Guns and Money, which he produced. Between 2023 and 2024, Cryer executive-produced 13 episodes of Extended Family and the short film David Again (2024).
Where is Jon Cryer Today?
Jon Cryer may not be dominating headlines like he did in the 2000s to mid-2010s, during the heydays of Two and a Half Men, but that’s largely his choice. He’s deliberately chosen a quieter, more intentional approach to his career. By focusing on roles that challenge him and the cause he believes in, Cryer has been able to avoid being typecast. His transition from sitcom staple to dramatic role is a testament to his versatility and talent.
Unlike in Two and a Half Men, these days, Jon Cryer is happily sporting a bald head with a full face of beard. He first revealed his hair loss struggles to Conan O’Brien on his Conan talk show in 2013. So, yes, his bald Lex Luthor wasn’t only a prop. Post-Two and a Half Men, Cryer has chosen to get rid of all the spray-ons and “elaborate illusions” it took to make it appear he had hair. Since 2019, Jon Cryer has walked around and acted with a bald head.
If you missed him in Big Time Adolescence, you definitely saw him wear his new look in Extended Family. Although he doesn’t have a major upcoming project (or any project) as of mid-2025, Cryer is far from retiring as an actor. Just like he surprisingly got cast in the Arrowverse as Lex Luthor, fans and admirers should not be surprised to see Jon Cryer make a major comeback, whether on the big or small screens.
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